There was a guy on Dennis Prager years ago who wrote a book about why presidents so often fail in foreign policy. The skills that get them ahead in American politics are those of persuading people who start out with mostly the same worldview. Sure there are political differences, but the vast majority of Americans agree on the basic rules we live under (at least until Obama). They agree that there should be elections, the bill of rights, etc. The skills that get them ahead in our system are persuasion, compromise, etc. They are good at it or they wouldn’t be elected.
So once they are elected and start to deal with other world leaders who share none of these values, they continue to operate in the same way. They think other people must be more or less like the people they have dealt with their whole career, and trust their abilities to succeed with them too. But people with vastly different worldviews are not going to react like Americans. They will take decency as weakness, and compromise as a temporary measure until they gain an advantage. This isn’t only liberals. Just think about G.W. Bush claiming to look into Putin’s soul, and believing that everyone in the world longs to live in a free society. It’s an inability or unwillingness to step outside their experience and understand the world from an alien point of view.
Good point. That also accounts for Chamberlain's failure with Hitler and FDR's failures with Stalin. Subsequent politicians learned from their mistakes.
Peters may have a point about the ticket punching mentality in government nowadays. There's an assumption that there's a specific set of things one has to do and a narrow range of opinions one can have in order to rise through the system.
Maybe outsiders who aren't just climbing the ladder by doing what they think they're supposed to do have a better understanding of foreign despots who also rose in unconventional -- indeed, brutal -- ways.